Diisopropylethylamine → Methyl 2-(4-ethyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate

HRID 1092167Notes

Reaction equation

HRID 1092167 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1.[CH2:12]([N:14]1[CH2:20][CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[CH3:13].C(N(C(C)C)C(C)C)C>ClCCl>[CH2:12]([N:14]1[CH2:20][CH2:19][CH2:18][N:17]([C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=2)[CH2:16][CH2:15]1)[CH3:13]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 75775381-Ethyl-1,4-diazepaneHCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

Product 1

HCID 66589959Methyl 2-(4-ethyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylateYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 2-chloropyrimidine-5-carboxylate (200 mg, 1.16 mmol) in dichloromethane (4.00 mL) was added to a stirred solution of 1-ethyl-1,4-diazepane (149 mg, 1.16 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (0.902 mL, 5.22 mmol) in dichloromethane (4.00 mL) at 25° C. The resulting solution was stirred at ambient temperature for 18 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (20 mL) and the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford methyl 2-(4-ethyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate (268 mg, 87%) as a cream oil which crystallised on standing. This was used directly with no further purification.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in MeOH (20 mL)
  3. customthe crude product was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-cf6d0cac24e3424ca40de2eb8bf69b42
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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